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Article

Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong?

University of Basel, Department of Chemistry, BPR 1096, Mattenstrasse 24a, CH-4058 Basel, Switzerland
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Author to whom correspondence should be addressed.
Academic Editor: Gianfranco Favi
Molecules 2019, 24(9), 1799; https://doi.org/10.3390/molecules24091799
Received: 15 April 2019 / Revised: 7 May 2019 / Accepted: 8 May 2019 / Published: 9 May 2019
(This article belongs to the Special Issue Modern Strategies for Heterocycle Synthesis)
The preparation of 24-functionalized 12,22:26,32-terpyridines (4′-functionalized 3,2:6′,3″-terpyridines) by the reaction of three 4-alkoxybenzaldehydes with 3-acetylpyridine and ammonia was investigated; under identical reaction conditions, two (R =nC4H9, C2H5) gave the expected products whereas a third (R = nC3H7) gave only a cyclohexanol derivative derived from the condensation of three molecules of 3-acetylpyridine with two of 4-(n-propoxy)benzaldehyde. A comprehensive survey of “unexpected” products from reactions of ArCOCH3 derivatives with aromatic aldehydes is presented. Three different types of alternative product are identified. View Full-Text
Keywords: terpyridines; 3,2′:6′,3″-terpyridine; cyclohexanol derivative; condensation; heterocyclic terpyridines; 3,2′:6′,3″-terpyridine; cyclohexanol derivative; condensation; heterocyclic
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MDPI and ACS Style

Rocco, D.; Housecroft, C.E.; Constable, E.C. Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong? Molecules 2019, 24, 1799. https://doi.org/10.3390/molecules24091799

AMA Style

Rocco D, Housecroft CE, Constable EC. Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong? Molecules. 2019; 24(9):1799. https://doi.org/10.3390/molecules24091799

Chicago/Turabian Style

Rocco, Dalila, Catherine E. Housecroft, and Edwin C. Constable. 2019. "Synthesis of Terpyridines: Simple Reactions—What Could Possibly Go Wrong?" Molecules 24, no. 9: 1799. https://doi.org/10.3390/molecules24091799

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